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Content Provider | Royal Society of Chemistry (RSC) |
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Author | Fazzi, Daniele Maciejewski, Jan Petraglia, Riccardo Claveau, Alexis Nicolai, Adrien Baudat, Emilie Corminboeuf, Clemence Cervini, Luca Miéville, Pascal Sobczuk, Adam Sforazzini, Giuseppe |
Copyright Year | 2017 |
Abstract | Here we present a molecular architecture that can reversibly change the geometric conformation of its π-system backbone via irradiation with two different wavelengths. The proposed ‘molecular actuator’ consists of a photoswitchable azobenzene orthogonally connected to a π-conjugated bithiophene by both direct and aliphatic linker-assisted bonding. Upon exposure to 350 nm light, the trans azobenzene moiety isomerizes to its cis form, causing the bithiophene to assume a semiplanar anti conformation (extended π-conjugation). Exposure to 254 nm light promotes the isomerization of the azobenzene unit back to its initial extended trans conformation, thus forcing the bithiophene fragment to twist out of coplanarity (restricted π-conjugation). The molecular conformation of the bithiophene was characterized using steady-state UV-vis and nuclear magnetic resonance spectroscopy, as well as ab initio computations. The proposed molecular design could be envisaged as a π-conjugation modulator, which has potential to be incorporated into extended linear π-systems, i.e. via the terminal α-thiophene positions, and used to tune their optical and electronic properties. |
Starting Page | 361 |
Ending Page | 365 |
Page Count | 5 |
File Format | HTM / HTML PDF |
ISSN | 20416520 |
Volume Number | 8 |
Issue Number | 1 |
Journal | Chemical Science |
DOI | 10.1039/c6sc03196j |
Language | English |
Publisher | Royal Society of Chemistry |
Access Restriction | Subscribed |
Subject Keyword | Aliphatic compound Isomerization Conformational isomerism Coplanarity Nuclear magnetic resonance spectroscopy Actuator Azobenzene Ab initio quantum chemistry methods |
Content Type | Text |
Resource Type | Article |
Subject | Chemistry |
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